1. Field of the Invention
The present invention relates to a phthalamide derivative or salt thereof, an agrohorticultural insecticide containing said compound as an active ingredient thereof, and a method for using the agrohorticultural agent.
2. Related Art
JP-A-61-180753 discloses some of the phthalamide derivatives of the present invention. However, in that patent application specification, there is neither disclosed nor suggested about usefulness of said derivatives as an agrohorticultural insecticide. Further, although similar compounds are disclosed in JP-A-59-163353 and J. C. S. Perkin I, 1338-1350 (1978), etc., there is made no mention nor suggestion in these publications about usefulness of those compounds as an agrohorticultural insecticide.
The present inventors have conducted extensive studies with the aim of developing a novel agrohorticultural agent. As a result, it has been found that the phthalamide derivatives of the present invention represented by general formula (I), which are novel compounds not found in literature, can be put to a novel use as an agrohorticultural insecticide comprising not only these novel compounds but also some known compounds disclosed in prior art. Based on this finding, the present invention has been accomplished.
The present invention relates to phthalamide derivatives represented by the following general formula (I) or salt thereof, an agrohorticultural insecticide containing, as active ingredients thereof, the phthalamide derivative represented by the general formula (I) or salt thereof and some known compounds, and a method for using the same: 
wherein A1 represents C1-C8 alkylene group, substituted C1-C8 alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, hydroxy C1-C6 alkyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, C3-C8 alkynylene group, or substituted C3-C8 alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group,
further, an arbitrary saturated carbon atom in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group, substituted C3-C8 alkenylene group, C3-C8 alkynylene group and substituted C3-C8 alkynylene group may be substituted with a C2-C5 alkylene group to form a C3-C6 cycloalkane ring, and arbitrary two carbon atoms in said C1-C8 alkylene group, substituted C1-C8 alkylene group, C3-C8 alkenylene group and substituted C3-C8 alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a C3-C6 cycloalkane ring or C3-C6 cycloalkene ring;
R1 represents hydrogen atom, mercapto group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A2xe2x80x94R4 [wherein A2 represents xe2x80x94C(xe2x95x90O)xe2x80x94, xe2x80x94C(xe2x95x90S)xe2x80x94, or xe2x80x94C(xe2x95x90NR5)xe2x80x94 (in which R5 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkoxy group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, C1-C6 alkoxycarbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group),
C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group; and
(1) in cases where A2 represents xe2x80x94C(xe2x95x90O)xe2x80x94, xe2x80x94C(xe2x95x90S)xe2x80x94 or xe2x80x94C(xe2x95x90NR5)xe2x80x94 wherein R5 is as defined above, R4 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94Z1xe2x80x94R6 wherein Z1 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94 or xe2x80x94N(R7)xe2x80x94 (wherein R7 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group or C1-C6 alkoxycarbonyl group), and R6 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and
(2) in cases where A2 represents C1-C8 alkylene group, halo C1-C8 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, R4 represents hydrogen atom, halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94Z2xe2x80x94R8 wherein Z2 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94N(R9)xe2x80x94 (wherein R9 represents hydrogen atom, C1-C6 alkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, phenylcarbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group and halo C1-C6 alkylsulfonyl group), xe2x80x94C(xe2x95x90O)xe2x80x94 or xe2x80x94C(xe2x95x90NOR10)xe2x80x94 (wherein R10 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C1-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group) and R8 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C6 alkylcarbonyl group, halo C1-C6 alkylcarbonyl group, C1-C6 alkoxycarbonyl group, mono C1-C6 alkylaminocarbonyl group, di C1-C6 alkylaminocarbonyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenyl C1-C4 alkyl group, substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group], or
alternatively, R1 may be combined with A1 to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;
R2 and R3 which may be same or different, represent hydrogen atom, C3-C6 cycloalkyl group or xe2x80x94A2xe2x80x94R4 wherein A2 and R4 are as defined above; or
alternatively, R2 may be combined with A1 or R1 to form a 5- to 7-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;
X which may be same or different, represents halogen atom, cyano group, nitro group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A3xe2x80x94R11 [wherein A3 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94, xe2x80x94SOxe2x80x94, xe2x80x94SO2xe2x80x94, xe2x80x94C(xe2x95x90O)xe2x80x94, xe2x80x94C(xe2x95x90NOR12)xe2x80x94 (in which R12 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, C3-C6 cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C1-C4 alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group), C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group; and
(1) in cases where A3 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94, xe2x80x94SOxe2x80x94 or xe2x80x94SO2xe2x80x94, R11 represents halo C3-C6 cycloalkyl group, halo C3-C6 cycloalkenyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A4xe2x80x94R13 (wherein A4 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C3-C6 alkenylene group, halo C3-C6 alkenylene group, C3-C6 alkynylene group or halo C3-C6 alkynylene group, and R13 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A5xe2x80x94R14 (wherein A5 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94, xe2x80x94SOxe2x80x94, xe2x80x94SO2 or xe2x80x94C(xe2x95x90O)xe2x80x94, and R14 represents C1-C6 alkyl group, halo C1-C6 alkyl group, C3-C6 alkenyl group, halo C3-C6 alkenyl group, C3-C6 alkynyl group, halo C3-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group)), and
(2) in cases where A3 represents xe2x80x94C(xe2x95x90O)xe2x80x94 or xe2x80x94C(xe2x95x90NOR12)xe2x80x94 wherein R12 is as defined above, R11 represents hydrogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, and
(3) in cases where A3 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, R11 represents hydrogen atom, hydroxy group, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A6xe2x80x94R15 (wherein A6 represents xe2x80x94Oxe2x80x94, xe2x80x94Sxe2x80x94, xe2x80x94SOxe2x80x94 or xe2x80x94SO2xe2x80x94, and R15 represents C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A7xe2x80x94R16 (wherein A7 represents C1-C6 alkylene group, halo C1-C6 alkylene group, C2-C6 alkenylene group, halo C2-C6 alkenylene group, C2-C6 alkynylene group or halo C3-C6 alkynylene group, and R16 represents hydrogen atom, halogen atom, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, cl-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group))]; and l represents an integer of 0 to 4; and
alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and
Y may be same or different and represents halogen atom, cyano group, nitro group, halo C3-C6 cycloalkyl group, tri C1-C6 alkylsilyl group in which C1-C6 alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, or xe2x80x94A3xe2x80x94R11 wherein A3 and R11 are as defined above; and m represents an integer of 0 to 5; and
Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group, heterocyclic group, and substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, halo C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, halo C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, halo C1-C6 alkylsulfonyl group, mono C1-C6 alkylamino group, di C1-C6 alkylamino group in which C1-C6 alkyl groups may be same or different, and C1-C6 alkoxycarbonyl group; and
n represents an integer of 0 to 2;
provided that when X, R2 and R3 simultaneously represent hydrogen atom, m represents an integer of 2, Y of the 2-position represents fluorine atom and Y of the 3-position represents chlorine atom, then A1 is not propylene group, R1 is not methyl group and n is not an integer of 0.
In the definition of the general formula (I) representing the phthalamide derivative of the present invention, the term xe2x80x9chalogen atomxe2x80x9d means chlorine atom, bromine atom, iodine atom or fluorine atom; the term xe2x80x9cC1-C6 alkylxe2x80x9d, means a straight or branched chain alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like; the term xe2x80x9chalo C1-C6 alkylxe2x80x9d means a straight or branched chain alkyl group having 1 to 6 carbon atoms which may be substituted with at least one, same or different halogen atoms; the term xe2x80x9cC1-C8 alkylenexe2x80x9d means a straight or branched chain alkylene group having 1 to 8 carbon atoms such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene and the like; the term xe2x80x9ca 5- to 8- or 5- to 7-membered ring which may be intercepted by 1 to 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms formed by R1 with A1, or R2 with A1 or R1xe2x80x9d means, for example, perhydrothiazine ring, thiazolidine ring, thiazetidine ring, dihydrothiazine ring, thiazoline ring, perhydroxathiazine ring, dihydroxathiazine ring, dithiazine ring, perhydrodithiazine ring, and the like.
The term xe2x80x9cheterocyclic groupxe2x80x9d means 5- to 6-membered heterocyclic group having one or more same or different hetero atoms selected from oxygen atoms, sulfur atoms or nitrogen atoms such as pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, trithiazolyl group, pyrazolyl group, and the like. As the xe2x80x9cfused ringxe2x80x9d, there can be exemplified naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, coumarone, isocoumarone, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole, indazole, and the like.
As a salt of a phthalamide derivative represented by the general formula (I) of the present invention, there can be exemplified inorganic acid salt such as hydrochlorate, sulfate, nitrate, phosphate and the like; organic acid salt such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salt of metallic ion such as sodium ion, potassium ion, calcium ion and the like.
Some of the phthalamide derivatives represented by the general formula (I) of the present invention contain an asymmetric carbon atom or an asymmetric center in the structural formula thereof, and in some cases there can exist two optical isomers. The present invention includes all these optical isomers and all the mixtures consisting of arbitrary proportions of these optical isomers.
Preferable examples of each substituent of the phthalamide derivative of general formula (I) or salt thereof of the present invention are A1 is a straight or branched C1-C8 alkylene group; R1 is C1-C6 alkyl group or halo C1-C6 alkyl group; each of R2 and R3 is hydrogen atom or C1-C6 alkyl group; X is halogen atom, nitro group, C1-C6 alkyl group, halo C1-C6 alkyl group or halo C1-C6 alkoxy group; and Y is halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group or halo C1-C6 alkoxy group.
The phthalamide derivatives of the present invention represented by the general formula (I) can be produced, for example, by the production processes mentioned below. 
wherein R1, R2, A1, X, Y, l, m and n are as defined above.
A phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-1) can be produced.
(1) General Formula (V)xe2x86x92General Formula (III)
As the inert solvent used in this reaction, any solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or as a mixture thereof.
Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess. If necessary, the reaction may be carried out under dehydrating conditions.
As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.
The phthalic anhydride derivative of the general formula (V) can be produced by the process described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1929), J. Am. Chem. Soc., 63, 1542 (1941), etc. The aniline of the general formula (IV) can be produced by the process described in J. Org. Chem., 29, 1 (1964), Angew. Chem. Int. Ed. Engl., 24, 871 (1985), Synthesis, 1984, 667, Bulletin of the Chemical Society of Japan, 1973, 2351, DE-2606982, JP-A-1-90163, etc.
(2) General Formula (III)xe2x86x92General Formula (I-1)
In this reaction, there can be used the inert solvents exemplified above as the inert solvent used in the reaction (1).
Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though the amine of the general formula (II) may be used in excess.
As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. 
wherein R1, R2, A1, X, Y, l, m and n are as defined above, Xxe2x80x2 is a halogen atom or a nitro group, provided that X is other than a hydrogen atom or a nitro group.
A phthalimide derivative of the general formula (III-1) is reacted with a reactant corresponding to X in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-1) can be produced.
(1) General Formula (III-1)xe2x86x92General Formula (III)
This reaction can be carried out according to the methods described in J. Org. Chem., 42, 3415 (1977), Tetrahedron, 25, 5921 (1969), Synthesis, 1984, 667, Chem. Lett., 1973, 471, J. Org. Chem., 39, 3318 (1974), J. Org. Chem., 39, 3327 (1974), etc.
(2) General Formula (III)xe2x86x92General Formula (I-1)
This reaction can be carried out according to production process 1-(2). 
wherein R1, R2, R3, A1, X, Y, l, m and n are as defined above.
A phthalic anhydride derivative of the general formula (V) is reacted with an amine of the general formula (II) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (III-4). The phthalamic acid (III-4) is treated as follows after or without isolation. When R2 of the phthalamic acid (III-4) is a hydrogen atom, the phthalamic acid (III-4) is condensed into a compound of the general formula (VI) in the presence of a condensing agent, and the compound (VI) is reacted with an aniline of the general formula (IVxe2x80x2) in the presence of an inert solvent after or without being isolated. When R2 of the phthalamic acid (III-4) is other than a hydrogen atom, the phthalamic acid (III-4) is condensed with an aniline of the general formula (IV) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.
Alternatively, a phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IVxe2x80x2) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (III-5). The phthalamic acid (III-5) is treated as follows after or without isolation. When R3 of the phthalamic acid (III-5) is a hydrogen atom, the phthalamic acid (III-5) is condensed into a compound of the general formula (VI-1) in the presence of a condensing agent, and the compound (VI-1) is reacted with an amine of the general formula (II) in the presence of an inert solvent after or without being isolated. When R3 of the phthalamic acid (III-5) is other than a hydrogen atom, the phthalamic acid (III-5) is condensed with an amine of the general formula (II) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.
(1) General formula (V) or general formula (VI-1)xe2x86x92General Formula (III-4) or General Formula (I), respectively
The desired compound can be produced by this reaction in the same manner as in production process 1-(2).
(2) General Formula (III-4) or General Formula (III-5)xe2x86x92General Formula (VI) or General Formula (VI-1), respectively
The desired compound can be produced by this reaction according to the method described in J. Med. Chem., 10, 982 (1967).
(3) General Formula (VI) or General Formula (V)xe2x86x92General Formula (I) or General Formula (VII-5), respectively
The desired compound can be produced by this reaction in the same manner as in production process 1-(2).
(4) General Formula (III-4) or General Formula (III-5)xe2x86x92General Formula (I)
The desired compound can be produced by reacting the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5) with the aniline of the general formula (IVxe2x80x2) or the amine of the general formula (II), respectively, in the presence of a condensing agent and an inert solvent. If necessary, the reaction can be carried out in the presence of a base.
The inert solvent used in the reaction includes, for example, tetrahydrofuran, diethyl ether, dioxane, chloroform and dichloromethane. As the condensing agent used in the reaction, any condensing agent may be used so long as it is used in usual amide synthesis. The condensing agent includes, for example, Mukaiyama reagent (e.g. 2-chloro-N-methylpyridinium iodide), 1,3-dicyclohexylcarbodiimide (DCC), carbonyldiimidazole (CDI) and diethyl phosphorocyanidate (DEPC). The amount of the condensing agent used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).
As the base usable in the reaction, there can be exemplified organic bases such as triethylamine, pyridine, etc. and inorganic bases such as potassium carbonate, etc. The amount of the base used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).
As to the reaction temperature, the reaction can be carried out in a temperature range of 0xc2x0 C. to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it ranges from several minutes to 48 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. 
wherein R1, R2, A1, X, Y, l, m and n are as defined above, and Hal is halogen atom. 
wherein R1, Y and m are as defined above.
A benzoyl halide of the general formula (VII) is reacted with an amine derivative of the general formula (II) or (IVxe2x80x2) in the presence of an inert solvent to obtain a benzamide of the general formula (VIII-1) or (VIII-2). The benzamide (VIII-1) or (VIII-2) is ortho-metallized with a metallic reagent such as butyllithium or the like and then directly reacted with an isocyanate of the general formula (IX-1) or (IX-2). Alternatively, the benzamide (VIII-1) or (VIII-2) is reacted with carbon dioxide to obtain a phthalamic acid of the general formula (III-4xe2x80x2) or (III-5xe2x80x2) and then treated in the same manner as in Production process 3-(1) to (4). Thus, a phthalamide derivative of the general formula (I) can be produced.
(1) General Formula (VII)xe2x86x92General Formula (VIII-1) or General Formula (VIII-2)
The desired compound can be produced according to the description of J. Org. Chem. 32, 3069 (1967), etc.
(2) General Formula (VIII-1) or General Formula (VIII-2)xe2x86x92General Formula (I)
The desired compound can be produced by converting a benzamide of the general formula (VIII-1) or (VIII-2) into an ortho-lithio compound according to the description of J. Org. Chem. 29, 853 (1964) and then reacted with an isocyanate of the general formula (IX-1) or (IX-2) at a temperature of xe2x88x9280xc2x0 C. to room temperature, whereby the desired compound can be produced.
(3) General Formula (VIII-1) or General Formula (VIII-2)xe2x86x92General Formula (III-4xe2x80x2) or General Formula (III-5xe2x80x2), respectively
The desired compound can be produced by the same conversion into an ortho-lithio compound as in (2), followed by introduction of carbon dioxide at a temperature of xe2x88x9280xc2x0 C. to room temperature.
After completion of the reaction, the desired compound is isolated from the reaction solution by the conventional method and, if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.
(4) General Formula (III-4xe2x80x2) or General Formula (III-5xe2x80x2)xe2x86x92General Formula (I)
The desired compound can be produced by the same procedure as in production process 3-(1) to (4). 
wherein R1, R2, R3, A1, X, Y, l, m and n are as defined above, provided that n cannot be an integer of 0.
A phthalamide derivative of the general formula (I-2) is reacted with an oxidant in the presence of an inert solvent, whereby a phthalamide derivative of the general formula (I-3) can be produced.
As the inert solvent used in this reaction, there can be exemplified halogenated hydrocarbons such as dichloromethane, chloroform, etc., aromatic hydrocarbon such as toluene, xylene, etc., acids such as acetic acid, etc., and alcohols such as methanol, ethanol, propanol, etc.
As the oxidant, there can be exemplified m-chloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (Oxon), hydrogen peroxide, etc. The amount of the oxidant may be properly selected in the range of 0.5 to 3 equivalents per equivalent of the phthalic acid diamide derivative of the general formula (I-2).
As to the reaction temperature, the reaction can be carried out in a temperature range of xe2x88x9250xc2x0 C. to the boiling temperature zone of the inert solvent used. Though the reaction time is varied depending on the reaction temperature and scale of the reaction, it is in the range of several minutes to 24 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method and, if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.